[ CAS No. 1075-34-9 ] {[proInfo.proName]}

Name: 1075-34-9|5-Bromo-2-methylindole|98%
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Quality Control of [ 1075-34-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1075-34-9 ]

Product Details of [ 1075-34-9 ]

CAS No. :	1075-34-9	MDL No. :	MFCD01863677
Formula :	C₉H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BJUZAZKEDCDGRW-UHFFFAOYSA-N
M.W :	210.07	Pubchem ID :	5003968
Synonyms :

Calculated chemistry of [ 1075-34-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.96
TPSA :	15.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	3.14
Log Po/w (WLOGP) :	3.24
Log Po/w (MLOGP) :	2.61
Log Po/w (SILICOS-IT) :	3.67
Consensus Log Po/w :	2.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.73
Solubility :	0.0395 mg/ml ; 0.000188 mol/l
Class :	Soluble
Log S (Ali) :	-3.14
Solubility :	0.152 mg/ml ; 0.000722 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.53
Solubility :	0.00621 mg/ml ; 0.0000296 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.28

Safety of [ 1075-34-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1075-34-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1075-34-9 ]
Downstream synthetic route of [ 1075-34-9 ]

[ 1075-34-9 ] Synthesis Path-Upstream 1~10

1
[ 95-20-5 ]
[ 1075-34-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: for 0.5 h; Cooling with ice Stage #2: at 20℃; for 4.5 h;	Step 1. 5-Bromo-2-methyl-7H-indoleTo a solution of 2-methyl-iH-indole (5.0 g, 38.12 mmol) in sulfuric acid (80 mL) was added Ag₂S0₄ (12.5 g, 40.06 mmol) with ice cooling, and the solution was stirred for 30 min. Then Br₂ (6.4 g, 40.05 mmol) was added to the solution dropwise over 30 min. After the solution was stirred for 4 h at room temperature, the reaction was then quenched by the addition of water/ice (300 mL). The reaction mixture was extracted with dichloromethane (3 x 200 mL) and the organic layers combined, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 5-bromo-2-methyl-7H-indole as a light brown solid (6 g, 75percent).LC/MS (ES, m/z): [M+H]⁺ 211.0'H-NMR (300 MHz, CDC1₃): δ 11.23 (s, 1Η), 7.56 (s, 1Η), 7.21 (d, / = 8.7 Hz, 1H), 7.07 - 7.09 (m, 1H), 6.11 (s, 1H), 2.38 (s, 3H)
59%	Stage #1: for 0.5 h; Cooling with ice Stage #2: With bromine In sulfuric acid at 20℃; for 4 h; Stage #3: With water In sulfuric acid	EXAMPLE 24 2,2,2-Trifluoro-1-(5-(3-(isopropyl(methyl)amino)-6-(1H-tetrazol-5-yl)quinoxalin-2-yl)-2-methyl-1H-indol-3-yl)ethanone Step 1. 5-Bromo-2-methyl-1H-indole To a solution of 2-methyl-1H-indole (5.0 g, 38.12 mmol) in sulfuric acid (80 ml) was added Ag₂SO₄(12.5 g, 40.06 mmol) with ice cooling, and the solution was stirred for 30 min. Then Br₂(6.4 g, 40.05 mmol) was added to the solution dropwise over 30 min. After the solution was stirred for 4 h at room temperature, the reaction was quenched by the addition of water/ice (300 ml). The reaction mixture was extracted with dichloromethane (3.x.200 ml) and the organic layers combined, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 5-bromo-2-methyl-1H-indole as a light brown solid (4.7 g, 59percent).LC/MS (ES, m/z): [M+H]⁺211.0¹H-NMR (300 MHz, CDCl₃): δ 11.23 (s, 1H), 7.56 (s, 1H), 7.21 (d, J=8.7 Hz, 1H), 7.07-7.09 (m, 1H), 6.11 (s, 1H), 2.38 (s, 3H)

Reference： [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 161
[2] Patent: US2012/225863, 2012, A1, . Location in patent: Page/Page column 28

2
[ 20357-20-4 ]
[ 56904-86-0 ]
[ 1075-34-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With triphenylphosphine In diphenylether at 260℃; for 1 h;	General procedure: In a 50 ml round bottom flask containing magnetic stir bar was charged with o-nitro benzaldehydes (2 mmol), phosphorane (2.2 mmol), triphenyl phosphine (4.6 mmol) and diphenyl ether (10 mL) and heated at 260 ^oC for 1 h. The reaction mass was then cooled to room temperature and poured on silica column. Products were isolated by eluting with petrolium ether to 3:1 pet ether: ethyl acetate.

Reference： [1] Tetrahedron Letters, 2018, vol. 59, # 19, p. 1851 - 1854

3
[ 267002-57-3 ]
[ 1075-34-9 ]

Reference： [1] Tetrahedron, 2012, vol. 68, # 15, p. 3172 - 3178

4
[ 106-40-1 ]
[ 1075-34-9 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 21, p. 6372 - 6377

5
[ 13061-96-6 ]
[ 1240045-42-4 ]
[ 1075-34-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2586 - 2590

6
[ 10075-50-0 ]
[ 74-83-9 ]
[ 1075-34-9 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 35, p. 11299 - 11305

7
[ 6872-06-6 ]
[ 1075-34-9 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 17, p. 3267 - 3276

8
[ 99847-70-8 ]
[ 1075-34-9 ]

Reference： [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2541,2550; engl. Ausg. S. 2504, 2511

9
[ 67-64-1 ]
[ 589-21-9 ]
[ 1075-34-9 ]

Reference： [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1954, vol. 297, p. 229,233
[2] Farmaco, Edizione Scientifica, 1954, vol. 9, p. 611,615

10
[ 1075-34-9 ]
[ 124-38-9 ]
[ 4583-55-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10476 - 10480[2] Angew. Chem., 2014, vol. 126, # 39, p. 10644 - 10648,5

[ 1075-34-9 ] Synthesis Path-Downstream 1~88

1
[ 99847-70-8 ]
[ 1075-34-9 ]

Reference： [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 2541,2550; engl. Ausg. S. 2504, 2511

2
[ 500-22-1 ]
[ 1075-34-9 ]
5-Bromo-2-methyl-3-(pyridin-3-ylmethyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylsilane; In methanol; dichloromethane; trifluoroacetic acid;	PREPARATION 8 5-Bromo-2-methyl-3-(3-pyridylmethyl)-1H-indole A solution of <strong>[1075-34-9]5-bromo-2-methyl-1H-indole</strong> (J. Chem. Soc., 1428 (1965)) (2.0 g) and 3-pyridinecarboxaldehyde (1.02 g) in dry dichloromethane (20 ml) was added dropwise over 10 minutes to a stirred solution of triethylsilane(3.30 g) in trifluoroacetic acid (20 ml) at 0° C. The solution was stirred at 0° C. for 30 minutes and then evaporated under vacuum, keeping the temperature below 35° C. The residue was dissolved in dichloromethane, and the solution was washed with 2N sodium hydroxide, water and dried (MgSO4). The solution was evaporated and the residue was chromatographed on silica gel, using dichloromethane/methanol (50:1) as eluent. The product fractions were combined and evaporated, and the residue was crystallized from ether to give the title compound (2.15 g), m.p. 188°-190° C. Found: C,59.62; H,4.43; N,9.26. C15 H13 BrN2 requires: C,59.82; H,4.35; N,9.30percent.

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 1529 - 1532
[2]Patent: US5744488,1998,A

3
[ 1075-34-9 ]
[ 99847-70-8 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 14264 - 14265
[2]Tetrahedron Letters,1993,vol. 34,p. 1529 - 1532

4
[ 1075-34-9 ]
[ 152431-65-7 ]
[ 74-88-4 ]
[ 765936-90-1 ]

Reference： [1]Molecular Crystals and Liquid Crystals,2005,vol. 430,p. 173 - 179

5
[ 1075-34-9 ]
[ 105-36-2 ]
[ 72016-68-3 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

6
[ 1075-34-9 ]
[ 68-12-2 ]
[ 17826-09-4 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2586 - 2590
[3]Green Chemistry,2019,vol. 21,p. 968 - 972

7
[ 1075-34-9 ]
[ 919295-65-1 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

8
[ 1075-34-9 ]
N-(5-bromo-2-methyl-1H-indol-3-ylmethyl)-hydroxylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

9
[ 1075-34-9 ]
2-(5-bromo-2-methyl-1H-indol-3-yl)-N-hydroxy-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

10
[ 1075-34-9 ]
[ 919295-67-3 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

11
[ 1075-34-9 ]
[ 919295-68-4 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

12
[ 1075-34-9 ]
1-benzenesulfonyl-5-bromo-3-bromomethyl-2-methyl-1H-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

13
[ 1075-34-9 ]
[ 919295-70-8 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

14
[ 1075-34-9 ]
N-(1-benzenesulfonyl-5-bromo-2-methyl-1H-indol-3-ylmethyl)N-hydroxyformamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

15
[ 1075-34-9 ]
[ 919295-69-5 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 10 - 20

16
[ 1075-34-9 ]
[4-(2-{3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-benzo[b]thiophen-3-yl)-cyclopent-1-enyl]-1,2-dimethyl-1H-indol-5-yl}-vinyl)-phenyl]-diphenyl-amine [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals,2005,vol. 430,p. 173 - 179

17
[ 1075-34-9 ]
diethyl-(4-{2-[4-(2-{3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-benzo[b]thiophen-3-yl)-cyclopent-1-enyl]-1,2-dimethyl-1H-indol-5-yl}-vinyl)-phenyl]-vinyl}-phenyl)-amine [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals,2005,vol. 430,p. 173 - 179

18
[ 1075-34-9 ]
[ 1079-43-2 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 4033 - 4035

19
[ 1075-34-9 ]
[ 1082-37-7 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 4033 - 4035

20
[ 1075-34-9 ]
2-[4-(2-methyl-1H-5-indolyl)phenyl]propanoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 307 - 312

21
[ 1075-34-9 ]
[ 103987-31-1 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 3267 - 3276

22
[ 1075-34-9 ]
5-acetyl-3-chloro-2-methylindole [ No CAS ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 3267 - 3276

23
[ 1075-34-9 ]
[ 181299-27-4 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 3267 - 3276

24
[ 106-40-1 ]
[ 1075-34-9 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 6372 - 6377

25
[ 5391-39-9 ]
[ 1075-34-9 ]
5-bromo-3-(4,5-dihydro-1H-imidazol-2-yl)-2-methyl-1H-indole hydrochloride [ No CAS ]

Reference： [1]Patent: EP1266897,2002,A2 .Location in patent: Page 49

26
[ 1075-34-9 ]
[ 24424-99-5 ]
[ 879887-22-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dmap; In acetonitrile; at 20℃; for 16h;	5-Bromo-2-methylindole (4.2 g, 200.0 mmol), di-t-butylcarbonate (4.37 g, 20 mmol), 4-dimethylaminopyridine (2.93 g, 24 mmol) and CH3CN (50 mL) were mixed and stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc (300 mL) and the organic solution was washed successively with water (50 mL), a 1N HCl solution (50 mL), a saturated NaHCO3 solution (2×50 mL) and brine (25 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford an oil (6.11 g, 99% yield): 1H NMR (CDCl3, 300 MHz): 7.98 (d, 1H, J=9), 7.56 (d, 1H, J=1), 7.32 (dd, H, J=9, 1), 6.27 (s, 1H), 2.60 (d, 3H, J=1), 1.69 (s, 9H).

Reference： [1]Patent: US2006/63799,2006,A1 .Location in patent: Page/Page column 8
[2]Organic Letters,2019,vol. 21,p. 5514 - 5518

27
[ 1075-34-9 ]
[ 292638-85-8 ]
[ 6163-58-2 ]
[ 546114-96-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine;palladium diacetate;	3-(2-Methylindol-5-yl)acrylic Acid Methyl Ester A mixture of <strong>[1075-34-9]5-bromo-2-methylindole</strong> (2.10 g, 10.0 mmol), methyl acrylate (1.08 g, 12.5 mmol), palladium acetate (23.2 mg, 0.1 mmol), tri(o-tolyl)phosphine (61.3 g, 0.2 mmol) and triethylamine (3.62 g, 35.8 mmol) was heated under argon in a heavy-walled Pyrex tube at 100° C. for 3 h. The cooled reaction mixture was diluted with DCM (60 mL) and distilled water (30 mL). The organic layer was washed with distilled water (3*25 mL). The aqueous is layer was extracted with DCM (25 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give a pale yellow solid. Purification by recrystallization with EtOAc gave a pale yellow powder (1.57 g; 73percent): mp 172-173° C.; Rf0.35 (C); Rf0.61 (E); numax (KBr): 3295, 1698, 1305, 1282, 1165, 975 cm-1; m/z (EI): 215.1, 184.1, 156.1, 77.2; deltaH (CDCl3, 400 MHz): 2.45 (3 H, s), 3.82 (3 H, s), 6.25 (1 H, s), 6.42 (1 H, d, J=16.0), 7.27 (1 H, d, J=8.0), 7.35 (1 H, d, J=8.0), 7.69 (1 H, s), 7.85 (1 H, d, J=16.0), 8.15 (1 H, bs); deltaC (CDCl3, 101 MHz): 14.0, 51.8, 101.5, 111.0, 114.5, 121.1, 121.4, 126.5, 129.7, 136.7, 137.7, 147.4, 168.6; m/z calculated for C13H13NO2: 215.0946 (M+), found 215.0945 (M+).

Reference： [1]Patent: US2003/114441,2003,A1

28
[ 1075-34-9 ]
[ 61676-62-8 ]
[ 594-19-4 ]
[ 837392-54-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	In tetrahydrofuran; ethyl acetate; pentane;	EXAMPLE 467A 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole A solution of <strong>[1075-34-9]5-bromo-2-methyl-1H-indole</strong> (5.04 g, 24 mmol) in THF (25 mL) was added dropwise to a suspension of potassium hydride (3.2 g, 24 mmol) in THF at 0° C. After fifteen minutes at 0° C., the solution was cooled to -78° C. and a t-butyl lithium solution (1.7 M in pentane, 28.2 mL, 48 mmol) was added dropwise via syringe while maintaining the temperature below -55° C. After an additional 15 minutes, the solution was cooled to -78° C. and treated with a 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (9.8 mL, 48 mmol) dropwise via syringe. The solution was stirred at -78° C. for 1.5 hours, allowed to warm to room temperature and quenched with saturated aqueous ammonium chloride. The solution was diluted with ethyl acetate and filtered to remove inorganic material. The filtrate was extracted with ethyl acetate. The combined organics were washed with brine, dried (MgSO4) and concentrated. The concentrate was purified by flash chromatography on silica gel using 10percent ethyl acetate/hexanes to give 3.9 g (63percent yield) of the desired product. MS (ESI(+)) m/e 258 (M+H)+.

Reference： [1]Patent: US2005/26944,2005,A1

29
[ 1075-34-9 ]
[W(CO)5(=C(CCPh)((1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyloxy))] [ No CAS ]
[ 1122006-91-0 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 2096 - 2097

30
[ 1075-34-9 ]
pentacarbonyl(methoxy(phenylethynyl)carbene)tungsten⁽⁰⁾ [ No CAS ]
(+/-)-7-bromo-3a-methyl-1-phenyl-4,8b-dihydro-3aH-cyclopenta[b]-indol-3-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 2096 - 2097

31
[ 1075-34-9 ]
C₁₅H₇ClO₆W [ No CAS ]
(+/-)-7-bromo-1-(4-chloro-phenyl)-3a-methyl-4,8b-dihydro-3aH-cyclopenta[b]-indol-3-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 2096 - 2097

32
[ 1075-34-9 ]
C₃₀H₂₇ClO₆W [ No CAS ]
[ 1122006-95-4 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 2096 - 2097

33
[ 445262-62-4 ]
[ 1075-34-9 ]
[ 1194486-25-3 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 8709 - 8712

34
[ 1075-34-9 ]
[ 1219741-42-0 ]
[ 1219741-76-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; N,N-dimethyl-formamide;tetrakis(triphenylphosphine) palladium(0); In water; at 150℃; for 0.166667h;Microwave irradiation;	Step A Methyl 5-[(6-chloro-5-(2-methyl-1H-indol-5-yl)-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate. K2CO3 (1M in water) (0.26 mL, 0.260 mmol) was added to a solution of <strong>[1075-34-9]5-bromo-2-methyl-1H-indole</strong> (21.5 mg, 0.096 mmol), Intermediate 13 (50 mg, 0.087 mmol) and Pd(PPh3)4 (8 mg) in DMF (1.5 ml). The reaction was heated at 150 C. under microwave irradiation for 10 min. Volatiles were removed, and the residue was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. Combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification by HPLC eluting with 20-80% MeCN:water afforded the desired product.

Reference： [1]Patent: US2010/81643,2010,A1 .Location in patent: Page/Page column 109

35
[ 1075-34-9 ]
[ 102-96-5 ]
[ 1227380-58-6 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 2981 - 2986

36
[ 13061-96-6 ]
[ 1240045-42-4 ]
[ 1075-34-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2586 - 2590

37
[ 1075-34-9 ]
[ 1228076-47-8 ]
Fmoc-Pro-[2-Me-5-Br-Trp]-OMe [ No CAS ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 2576 - 2579

38
[ 1075-34-9 ]
[ 106-96-7 ]
5-bromo-2-methyl-1-(prop-2-ynyl)-1H-indole [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 6813 - 6816
[2]Chemistry - A European Journal,2010,vol. 16,p. 11827 - 11831

39
[ 110-91-8 ]
[ 1075-34-9 ]
[ 1268716-47-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With lithium hexamethyldisilazane;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In tetrahydrofuran; at 80℃;Inert atmosphere;	Example 6 Preparation of (E)-3-{3-fluoro-4-[3-(2-methyl-5-morpholin-4-yl-1H-indol-3-yl)-piperidin-1-ylmethyl]-phenyl}-N-hydroxy-acrylamide (4) To a mixture of <strong>[1075-34-9]5-bromo-2-methyl-1H-indole</strong> (4.40 g, 21 mmol) and morpholine (2.19 g, 25.1 mmol) in tetrahydrofuran (100 mL) is added a solution of lithium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 46.1 mmol) followed by (2'-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (330 mg, 0.838 mmol). The resulting mixture is purged with nitrogen, treated with Pd2(dba)3 (192 mg, 0.210 mmol), and heated at 80° C. overnight. The reaction mixture is cooled to room temperature, concentrated and purified by a silica gel column chromatography to give 2-methyl-5-morpholin-4-yl-1H-indole (4.30 g, 95percent yield). MS (m/z): 216.97 (M+1).
95%	With lithium hexamethyldisilazane; DavePhos;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 80℃;Inert atmosphere;	To a mixture of 5-bromo-2-methyl- l H-indole (4.40 g, 21 mmol) and morpholine(2.19 g, 25. 1 mmol) in tetrahydrofuran ( 100 mL) is added a solution of lithiumbis(trimethylsilyl)amide ( 1 .0 in tetrahydrofuran, 46.1 mmol) followed by (2'- dicyclohexylphosphanyl-biphenyl-2~yl)-dimethyl-amine (330 mg, 0.838 mmol). The resulting mixture is purged with nitrogen, treated with Pd2(dba)3 ( 1 2 mg, 0.210 mmol), and heated at 80°C overnight. The reaction mixture is cooled to room temperature, concentrated and purified by a silica gel column chromatography to give 2-methyl-5-morpholin-4-yi- l H-indole (4.30 g, 95percent yield). MS (m/z): 216.97 (M+ 1 ).

Reference： [1]Patent: US2011/53925,2011,A1 .Location in patent: Page/Page column 22-23
[2]Patent: WO2012/25155,2012,A1 .Location in patent: Page/Page column 40

40
[ 1075-34-9 ]
[ 73183-34-3 ]
[ 837392-54-8 ]

Yield	Reaction Conditions	Operation in experiment
33%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃;	Potassium acetate (477 mg, 4.76 mmol) was added to a solution of 5-bromo-2- methylindole (500 mg, 2.4 mmol), bis(pinacolato)diboron (725 mg, 2.86 mmol), and [1 ,1 '-bis-(diphenylphosphino)ferrocene]-dichloropalladium (II) dcm complex (178 mg, 0.24 mmol) in 1 ,4-dioxane (25 mL) in a 20 mL vial. The vial was capped and heated to 80°C, reaction was heated at this temperature with stirring overnight.The reaction mixture was concentrated, dissolved in EtOAc, and filtered through a 5g silica plug. This filtrate was concentrated and purified on an 80g silica column using 0- 10percent ethyl acetate in hexanes to furnish 202mg (33percent) of a clear colorless oil. LCMS m/z 258.3 (M+1 ) 1 H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.39 (s, 21 H) 2.40 (s, 3 H) 6.24 (s, 1 H) 7.25 (d, J=8.20 Hz, 1 H) 7.60 (d, J=8.20 Hz, 1 H) 7.94 (br. s., 1 H) 8.08 (s, 1 H)

Reference： [1]Patent: WO2011/73845,2011,A1 .Location in patent: Page/Page column 67

41
[ 1075-34-9 ]
[ 1312473-61-2 ]

Reference： [1]Patent: WO2011/73845,2011,A1

42
[ 1075-34-9 ]
(R)-5-bromo-2-methylindoline [ No CAS ]
(S)-5-bromo-2-methylindoline [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 10661 - 10664

43
[ 1075-34-9 ]
[ 1246375-65-4 ]

Reference： [1]Patent: US2012/28963,2012,A1
[2]Patent: EP2412706,2012,A2

44
[ 1075-34-9 ]
[ 1246375-66-5 ]

Reference： [1]Patent: US2012/28963,2012,A1
[2]Patent: EP2412706,2012,A2

45
[ 1075-34-9 ]
[ 1246375-59-6 ]

Reference： [1]Patent: US2012/28963,2012,A1
[2]Patent: EP2412706,2012,A2

46
[ 1075-34-9 ]
[ 1246374-85-5 ]

Reference： [1]Patent: US2012/28963,2012,A1
[2]Patent: EP2412706,2012,A2

47
[ 1075-34-9 ]
[ 24067-17-2 ]
[ 1246375-58-5 ]

Yield	Reaction Conditions	Operation in experiment
	(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 120℃;Microwave irradiation;	Compound 296; N-hydroxy-7-(N-(4-(2-methyl-1H-indol-5-yl)phenyl)methylsulfonamido)heptanamide; As shown in reaction scheme 4,6-bromo-2-methyl-1H-indole and 4-nitrophenylboronic acid were subjected to the Suzuki reaction to obtain compound 2, which was then reduced with palladium/activated carbon to obtain compound 3. Then, compound 3 is allowed to react with ethyl 7-bromoheptanoate to obtain compound 4, which was then allowed to react with methanesulfonyl chloride to obtain a compound of formula V-1, after which the compound of formula V-1 (16 mg, 0.035 mmol) was stirred with hydroxylamine and potassium hydroxide for 30 minutes. Then, a 50percent water solution of hydroxylamine was added to the stirred solution until the undissolved solids were dissolved so that the solution became clear. Then, the reaction solution was stirred at mom temperature for 10 hours, and after the completion of the reaction has been confirmed, the reaction product was concentrated under reduced pressure to remove the solvent. The remaining material was extracted using ethyl acetate, washed with brine, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized, thus obtaining compound 296 (12 mg, 77.3percent).1H NMR (400 MHz, CD3OD) delta 7.67 (d, J=1.9 Hz, 2H), 7.65 (s, 1H), 7.41 (d, J=6.6 Hz, 2H), 7.30 (d, J=3.5 Hz, 2H), 6.17 (s, 1H), 3.71 (t, J=6.7 Hz, 2H), 2.93 (s, 3H), 2.42 (s, 3H), 2.05 (t, J=7.3 Hz, 2H), 1.57 (m, 4H), 1.31 (m, 4H). MS (ESI) m/z 443 (M++H).
	(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 120℃;Microwave;	As shown in reaction scheme 4, 6-bromo-2-methyl-1H-indole and 4-nitrophenylboronic acid were subjected to the Suzuki reaction to obtain compound 2, which was then reduced with palladium/activated carbon to obtain compound 3. Then, compound 3 is allowed to react with ethyl 7-bromoheptanoate to obtain compound 4, which was then allowed to react with methanesulfonyl chloride to obtain a compound of formula V-1, after which the compound of formula V-1 (16 mg 0.035 mmol) was stirred with hydroxylamine and potassium hydroxide for 30 minutes. Then, a 50percent water solution of hydroxylamine was added to the stirred solution until the undissolved solids were dissolved so that the solution became clear. Then, the reaction solution was stirred at room temperature for 10 hours, and after the completion of the reaction has been confirmed, the reaction product was concentrated under reduced pressure to remove the solvent. The remaining material was extracted using ethyl acetate, washed with brine, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized, thus obtaining compound 296 (12 mg, 77.3percent). 1H NMR (400 MHz, CD3OD) delta 7.67 (d, J = 1.9 Hz, 2H), 7.65 (s, 1H), 7.41 (d, J = 6.6 Hz, 2H), 7.30 (d, J = 3.5 Hz, 2H), 6.17 (s, 1H), 3.71 (t, J = 6.7 Hz, 2H), 2.93 (s, 3H), 2.42 (s, 3H), 2.05 (t, J = 7.3 Hz, 2H), 1.57 (m, 4H), 1.31 (m, 4H). MS (ESI) m/z 443 (M+ + H).

Reference： [1]Patent: US2012/28963,2012,A1 .Location in patent: Page/Page column 24
[2]Patent: EP2412706,2012,A2 .Location in patent: Page/Page column 40-41

48
[ 267002-57-3 ]
[ 1075-34-9 ]

Reference： [1]Tetrahedron,2012,vol. 68,p. 3172 - 3178

49
[ 445262-62-4 ]
[ 1075-34-9 ]
[ 1194486-25-3 ]
[ 1372797-81-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 3202 - 3209

50
[ 1075-34-9 ]
[ 1383843-51-3 ]